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Seeds Of Terror PDF Free Download

The following is a listing of commercially released books from Pinnacle Entertainment Group and licensees for the Savage Worldsrole-playing and miniatures game. This does not include various free downloads. Accessories such as card decks, screens and miniatures are also not listed.

Operation Condor: The internationalization of terror1 Dr. Leonardo Marmontel Braga2 “Many people can hardly admit that the world lives in a permanent war situation”, Bacigalupo, a Chilean General from the Academia Superior de Seguridad Nacional in the first number of the journal Seguridad Nacional (National Security) in: Comblin, 1978: 32; free translation from the original passage in Spanish. Download Bein Connect for PC free at BrowserCam. Il est scandaleux que l'on puisse pas Snip2Code – Telecharger Bein Sport Sur Pc Gratuit Softonic 13.

Great White Games/Pinnacle Entertainment Group[edit]

Core rules[edit]

  • Savage Worlds: Fast! Furious! Fun! (SW) (1st Edition, 2003; hardcover. Revised Edition, 2004; hardcover)
  • Savage Worlds: Explorer's Edition (SWEX[1])(1.5 Edition, 2007; digest-sized softcover)
  • Savage Worlds: Deluxe Edition (SWD) (2nd Edition, 2011; hardcover)
  • Savage Worlds: Deluxe Explorer's Edition (SWDEE) (2.1 Edition, 2012; digest-sized softcover)
  • Savage Worlds: Adventure Edition (SWADE) (2.2 Edition, 2019; hardcover. 2.2 Edition {version 4.2}, 2019; PDF.)

Savage Settings series[edit]

  • Evernight: The Darkest Setting of All (2003; hardcover)
  • East Texas University / Degrees of Horror (2014; hardcover)
  • 50 Fathoms: High Adventure in a Drowned World (2003; hardcover)
  • 50 Fathoms Companion (2004; PDF)
  • Necessary Evil: Supervillains Must Rise Where Heroes Fall (2004; hardcover)
  • Low Life: The Rise of the Lowly (2005; hardcover)
  • Rippers: Horror Roleplaying in the Victorian Age (2005; hardcover)
  • Rippers Companion (2007; PDF)
  • The Savage World of Solomon Kane (2007; hardcover)
  • Solomon Kane: Travelers' Tales (2008; softcover)
  • The Savage Foes of Solomon Kane (2010; hardcover)
  • Slipstream (2008; hardcover)
  • Necessary Evil: Explorer's Edition (2009; softcover)
  • Solomon Kane Bennies (2009)
  • Necessary Evil Bennies (2010)
  • Slipstream Bennies (2010)
  • Lankhmar: City of Thieves (2015: hardcover)
  • Lankhmar: Savage Seas of Nehwon (2018: hardcover)
  • The Savage World of Flash Gordon RPG (2018; Hardback)
  • The Savage World of Flash Gordon: Kingdoms of Mongo (2018; Hardback)

Weird Wars[edit]

  • Tour of Darkness (2004; hardcover)
  • Necropolis 2350 (2006; softcover)
  • Weird War Two (2009; hardcover)
  • Weird War Two Bennies (2009)
  • Weird Wars Rome (2013)
  • Weird War One (2016)

Deadlands[edit]

  • Deadlands: Reloaded! (2006; hardcover)
  • Deadlands: Coffin Rock (2008; softcover)
  • Deadlands: The Flood, Plot Point Campaign (2009; PDF, hardcover)
  • Deadlands: The Flood Player's Guide (2009; free PDF)
  • Deadlands: Marshal's Screen / Murder on the Hellstromme Express adventure (2009; hardcover gamemaster's screen, softcover booklet)
  • Deadlands: Don't Drink the Water (2009; PDF)
  • Deadlands: Murder on the Hellstromme Express (2009; PDF)
  • Deadlands Fate Chips (2009)
  • Deadlands: Saddle Sore (2010; PDF)
  • Deadlands Trail Guide: South o' the Border (2010; PDF)
  • Deadlands Player's Guide (2010; 2nd Printing; hardcover)
  • Deadlands Marshal's Handbook (2010; 2nd Printing; hardcover)
  • Deadlands: For Whom the Whistle Blows–Night Train 2 (2010; PDF)
  • Deadlands Trail Guide: The Great Northwest (2010; PDF)
  • Deadlands: The 1880 Smith & Robards Catalog (2011; PDF/softcover)
  • Deadlands Trail Guide: Weird White North (2011; PDF)
  • Deadlands: Devil's Night (2011; free PDF)
  • Deadlands Player's Guide (2012; 3rd Printing; softcover)
  • Deadlands Marshal's Handbook (2012; 3rd Printing; softcover)
  • Deadlands: The Last Sons, Plot Point Campaign (2012; PDF, hardcover)
  • Deadlands: The Last Sons Player's Guide, (2012; free PDF)
  • Deadlands: Guess Who's Coming to Donner (2012; PDF)
  • Deadlands: Trail Guides, Volume I (2012; PDF/softcover)
  • Deadlands: Return to Manitou Bluff (2012; PDF/softcover)
  • Deadlands: Bad Times on the Goodnight (Blood Drive I) (2012; PDF)
  • Deadlands: Temple of the Sun (Map Pack 1) (2012; PDF)
  • Deadlands: High Plains Drovers (Blood Drive II) (2012; PDF)
  • Deadlands: Ghost Towns (2012; PDF/softcover)
  • Deadlands: Range War! (Blood Drive III) (2012; PDF)

Deadlands: Hell on Earth[edit]

  • Deadlands: Hell on Earth Reloaded (2012; PDF, hardcover)

Deadlands Noir[edit]

  • Tenement Men (Kickstarter Exclusive Dime Novel) (2012; PDF)

Standalone RPGs[edit]

  • Pirates of the Spanish Main (2007; hardcover)
  • Space 1889: Red Sands (2010; hardcover)
  • The Sixth Gun Role-Playing Game (2015; hardcover & Paperback)

Skirmishes[edit]

  • Rippers: The Horror Wars (2004; softcover)
  • Modern Ops (2005; print-on-demand)

Genre toolkits[edit]

  • Fantasy Bestiary Toolkit (2005)
  • Fantasy Gear Toolkit (2005)
  • Fantasy World Builder Toolkit (2005)
  • Fantasy Character Generator Toolkit (2005)
  • Science Fiction Bestiary Toolkit (2005)
  • Science Fiction Gear Toolkit (2006)
  • Science Fiction World Builder Toolkit (2006)
  • Pulp Gear Toolkit (2006)
  • Pulp GM's Toolkit (2006)
  • Horror Bestiary Toolkit (2006)
  • Horror Companion (2011)
  • Horror GM's Toolkit (2007)
  • Fantasy Companion (2009; softcover)
  • Science Fiction Companion (2013)
  • Super Powers Companion (2009; softcover)
  • Super Powers Companion: Second Edition (2013)
  • Horror Companion (2012; softcover)

Adventures[edit]

  • Privateer's Bounty (2003)
  • Screamers (2003)
  • On the Rocks (2003)
  • Rise Alabama (2004)
  • Noble Deceit (2004)
  • Zombie Run (2004)
  • Highwater War (2004)
  • Smugglers Cove (2004)
  • Prisoner of Pain (2004)
  • Through the Cathode Ray Tube (2005)
  • The Black Ankh (2005)
  • Tales of the Forlorn Hope (2006)
  • The Third Hand (2006)
  • The Templar Legacy (2008)
  • Death on the Dartmoor (2008)
  • The Night of Thoth (2008)
  • Heart of Steel (2009)
  • Bayonets, Buttons, & Blood (2009)
  • Weird Wars: Island of Dreams (2011)

Adamant Entertainment[edit]

Setting[edit]

  • MARS (2009; PDF and softcover)
  • Thrilling Tales (2009; PDF and softcover)

Atomic Overmind Press[edit]

Setting[edit]

  • The Day after Ragnarok (2009; PDF and softcover)

Battlefield Press, Inc[edit]

Settings[edit]

  • Sherwood: The Legend of Robin Hood (2009; PDF and softcover)
  • Gaslight Victorian Fantasy (2009; PDF and softcover)
  • Eldritch Skies (2014; PDF and hardcover)

Supplement[edit]

  • Distant Vistas (2014; PDF and hardcover)

FunSizedGames[edit]

Setting[edit]

  • Streets of Bedlam: A Savage World of Crime + Corruption (2012; PDF and softcover)

Adventure[edit]

  • Streets of Bedlam: Five-Story Drop (2013; PDF and softcover)

Melior Via[edit]

Setting[edit]

  • Accursed (2013; PDF and hardcover)

Supplement[edit]

  • World of Morden (2016; softcover and hardcover)

Adventure[edit]

  • Ill Omens (2014; softcover)

GG Studio[edit]

Settings[edit]

  • Enascentia (2013; PDF and softcover)
  • Freak Control (2014; PDF and softcover)
  • Ultima Forsan (2014; PDF and softcover)
  • Warage - L'Alba degli Eroi (2014; PDF and softcover)

Supplements[edit]

  • Deadlands: Messico & Nuvole (2014; PDF and softcover)
  • Enascentia - Dietro lo Schermo (2014; PDF and softcover)

Triple Ace Games[edit]

Settings[edit]

  • Necropolis 2350 (2008; hardcover)
  • Sundered Skies (2008; hardcover)
  • Necropolis 2350: 2351-55 Update (2009; PDF and softcover)
  • Hellfrost Player's Guide (2009; hardcover)
  • Hellfrost Bestiary (2009; hardcover)
  • Hellfrost Gazetteer (2009; hardcover)
  • Sundered Skies Companion (2010; PDF and softcover)
  • Hellfrost Encounters Book 1 (2010; PDF and hardcover)
  • Hellfrost Expansion (2010; PDF and softcover)
  • Wonderland No More (2011; softcover)

Genre toolkits[edit]

  • Savage Worlds Handbook: Perilous Places & Serious Situations (2008; PDF)

Adventures[edit]

Daring Tales of Adventure[edit]

  • #1: To End All Wars and Chaos on Crete (2008; PDF)
  • #2: Web of the Spider Cult (2008; PDF)
  • #3: Treasure of the Templars (2008; PDF)
  • #4: The Talons of Lo-Peng (2008; PDF)
  • #5: Sky Pirates of the Caribbean (2008; PDF)
  • #6: The Palladium Peril (2008; PDF)
  • #7: The Twelfth Gate (2008; PDF)
  • #8: Terror of the Z-Bomb (2008; PDF)
  • #9: Island of Terror (2009; PDF)
  • #10: Kingdom of the Blood Gods (2009; PDF)
  • #11: The Hands of Kali (2009; PDF)
  • #12: Legacy of Tunguska (2009; PDF)
  • #13: The Devil's Chalice (2009; PDF)
  • #14: The Sword of Avalon (2009; PDF)
  • #15: The Muramasa Curse (2009; PDF)
  • #16: Empire of the Black Pharaoh (2009; PDF)
  • Compendium #01 (2009; Softback)
  • Compendium #02 (2009; Softback)
  • Compendium #03 (2009; Softback)
  • Compendium #04 (2010; Softback)
  • Xmas DTA Special 2008: The Tale of the Fabulous Four (2008; PDF)
  • Xmas DTA Special 2009: Rocket Nazis on the Orient Express (2009; PDF)

Daring Tales of Chivalry[edit]

  • #1: A Knight's Tale (2008; PDF)
  • #2: Death at the Joust (2008; PDF)
  • #3: The Danbury Curse (2009; PDF)
  • #4: Castle Fairstone & The Madness of Sir Stephen (2009; PDF)

Daring Tales of the Space Lanes[edit]

  • #1: Waylaid on Wayland & Gunboat Diplomacy (2009; PDF)
  • #2: Bad Debts (2009; PDF)
  • #3: Robot Rumble (2009; PDF)
  • #4: The Last Journey of The Exodus (2009; PDF)
  • #5: The Black Guardian (2010; PDF)
  • #6: The Stealer of Light (2010; PDF)
  • #7: Deadly Chant (2010; PDF)

Hellfrost[edit]

  • N1: Lair of the Vermin Lord (2009; PDF)
  • N2: The Dark Seed (2009; PDF)
  • N3: Shadow of Darkness (2009; PDF)
  • N4: Pirates of the Crystalflow (2009; PDF)
  • N5: The Eoster Festival (2010; PDF)
  • S1: The Siege of Watchgap Fort (2009; PDF)
  • S3: Descent Into Madness (2009; PDF)
  • S2: The Lost City of Paraxus (2009; PDF)
  • V1: The Heart of Winter (2009; PDF)
  • V2: Against the Elements (2009; PDF)
  • S4: The Ice Fiend and Other Tales (2010; PDF)
  • V3: The Web of Deceit (2010; PDF)
  • H1: Sins of the Father (2010; PDF)
  • H2: The Blood of Godhammer (2010; PDF)
  • L1: The Frost Giant's Hold (2010; PDF)
  • S5: The Fey Tower and The Deadly Glade (2011; PDF)
  • V4: Death in the Mire (2011; PDF)
  • H3: The Blood Tide (2011; PDF)
  • Compendium #1: Saga of the Frost Giants (2011; softcover)
  • Compendium #2: Novice Adventures (2011; softcover)

Necropolis 2350[edit]

  • Tales from the Frontline #01 (2008; PDF)
  • The Long Sleep (2008; PDF)
  • The Last Word (2008; PDF)
  • The Broken Seal (2009; PDF)
  • Tales from the Frontline #02 (2009; PDF)
  • Opener of the Ways (2010; PDF)
  • Echoes (2010; PDF)

Sundered Skies[edit]

  • The Ice Tower (2008; PDF)
  • Fate of the Summoner (2008; PDF)
  • Blade of Destiny (2008; PDF)
  • Mind Thief (2009; PDF)
  • The Race (2009; PDF)
  • Within the Skies (2010; PDF)
  • Mists of Savannah (2010; PDF)

Wonderland No More[edit]

  • Egg of Seven Parts (2008; PDF)

Supplements[edit]

Daring Tales of Adventure[edit]

  • Daring Tales Guide to Rocket Rangers (2011; PDF)
  • Daring Tales Guide to Elite Nazi Units (2011; PDF)

Daring Tales of the Space Lanes[edit]

  • Sector 01 (2010; PDF)
  • Combat Hazards (2010; PDF)

Hellfrost[edit]

  • Hellfrost Calendar (2010; PDF)
  • Region Guide #1: Sacred Places (2010; PDF)
  • Region Guide #2: The Liche Lands (2010; PDF)
  • Region Guide #3: The Magocracy (2010; PDF)
  • Region Guide #4: Orcmark (2010; PDF)
  • Region Guide #5: Vestmark (2010; PDF)
  • Region Guide #6: The Withered Lands (2010; PDF)
  • Region Guide #7: Shattered Moor (2010; PDF)
  • Region Guide #8: The Ten Seas (2010; PDF)
  • Region Guide #9: Drachenlands (2010; PDF)
  • Region Guide #10: Heligioland (2010; PDF)
  • Region Guide #11: Ertha's Realm (2010; PDF)
  • Region Guide #12: Witchwood (2010; PDF)
  • Region Guide #13: Royalmark (2010; PDF)
  • Region Guide #14: Veermark (2010; PDF)
  • Region Guide #15: Crystalflow Confederacy (2010; PDF)
  • Region Guide #16: Alantaris Isle (2010; PDF)
  • Region Guide #17: The Great Swamp (2010; PDF)
  • Region Guide #18: The Freelands (2010; PDF)
  • Region Guide #19: Unclaimed Lands (2010; PDF)
  • Region Guide #20: The Mistlands (2010; PDF)
  • Region Guide #21: Chalcis (2010; PDF)
  • Region Guide #22: Midmark (2010; PDF)
  • Region Guide #23: The Battlelands (2010; PDF)
  • Region Guide #24: Aspiria (2010; PDF)
  • Region Guide #25: Ostmark (2010; PDF)
  • Region Guide #26: Nordmark (2010; PDF)
  • Region Guide #27: Angmark (2010; PDF)
  • Region Guide #28: Blackstone Barony (2010; PDF)
  • Region Guide #29: Barony of Cul (2010; PDF)
  • Region Guide #30: Barony of Trond (2010; PDF)
  • Region Guide #31: Cairn Lands (2010; PDF)
  • Region Guide #32: Coglelund (2010; PDF)
  • Region Guide #33: Freetown (2010; PDF)
  • Region Guide #34: The Frozen Forest (2010; PDF)
  • Region Guide #35: Giant's Throne (2011; PDF)
  • Region Guide #36: The Glittersands (2011; PDF)
  • Region Guide #37: Heldalund (2011; PDF)
  • Region Guide #38: Icedale Freeholds (2011; PDF)
  • Region Guide #39: Lakeland (2011; PDF)
  • Region Guide #40: The Vale (2011; PDF)
  • Region Guide #41: Seithrby (2011; PDF)
  • Region Guide #42: Sutmark (2011; PDF)
  • Region Guide #43: Angarion (2011; PDF)
  • Region Guide #44: The Borderlands (2011; PDF)
  • Region Guide #45: The Abyss (2011; PDF)
  • Region Guide #46: Godsheim (2011; PDF)
  • Region Guide #47: Isles of the Seareavers (2011; PDF)
  • Resource Management (2011; PDF)
  • Heroes & Villains 1 (2011; PDF)
  • Heroes & Villains 2: Spellcasters (2011; PDF)
  • Creature Guide Bufomi (2011; PDF)
  • Creature Guide Kreana (2011; PDF)

Seeds Of Terror Pdf Free Download Free

Daring Entertainment[edit]

Settings[edit]

Dawn of Legends[edit]

  • Dawn of Legends (2009; PDF and softcover)
  • Dawn of Legends Support Bundle (2009; PDF)

War of the Dead[edit]

  • War of the Dead: Chapter One (2010; PDF and softcover)
  • War of the Dead: Chapter Two (2011; PDF and softcover)
  • War of the Dead: Chapter Three (2011; PDF and softcover)
  • War of the Dead: Chapter Four (2012; PDF and softcover)

Super Powers Unleashed[edit]

  • Super Powers Unleashed (2017; PDF and softcover)

Adventures[edit]

  • G.E.T. Into Action: The Rising Storm (2009; PDF)
  • War of the Dead: Dead of Night (2010; PDF)
  • War of the Dead: Food For Thought (2010; PDF)
  • War of the Dead: Outbreak at Hopewell (2010; PDF)
  • Super Heroes Unleashed: Little Tin Gods (2017; PDF)

Supplements[edit]

Seeds

Seeds Of Terror Pdf Free Download Torrent

  • War of the Dead: The Paper Dead (Set 1) (2010; PDF)
  • War of the Dead: Fan-Created Support (2010; PDF)
  • War of the Dead: The Survivors (2010; PDF)
  • War of the Dead: Values of Survival (2010; PDF)
  • War of the Dead: The Survivors (Part 2) (2010; PDF)
  • War of the Dead: The Digital Dead (2011; PDF)

Evil DM Productions[edit]

Source book[edit]

  • Legends of Steel (2009; hardcover)

Gun Metal Games[edit]

Settings[edit]

  • Interface Zero (2010; PDF and hardcover)
  • Totems of the Dead: Player's Guide to the Untamed Lands (2011; PDF and hardcover)
  • Totems of the Dead: Game Master's Guide (2011; PDF and hardcover)
  • Interface Zero 2.0 (2014; PDF and hardcover)

Happy Monster Press[edit]

Settings[edit]

  • Children of the Apocalypse (2018; PDF and print-on-demand)
  • Legion of Liberty: Superheroes of 1776 (2019; PDF and print-on-demand)

Legion Publishing[edit]

Adventures[edit]

  • Savage Features #1: Out of Sight (2004)
  • Savage Features #2: The Last Round (2005)
  • Savage Features #3: They Came From Beyond Space (2005)
  • World of Meridian #1 - The Hunt (2005)
  • World of Meridian #2 - All that Glisters (2006)
  • World of Meridian #3 - Neveredge Falls (2003/2006)

Deadlands adventures and source books[edit]

  • Deadlands Dime Novel #1 - Beast of Fire (2005; print-on-demand)
  • Deadlands Dime Novel #2 - Deadshot (2006; print-on-demand)
  • Deadlands Dime Novel #3 - Frostbite (2006; print-on-demand)
  • Deadlands Territory Guide - Newfoundland: Rock of Ages (2004)

Weird Wars adventures[edit]

  • Weird War II Mission Manual #1 - Bridge Across Time (2004)
  • Weird War II Mission Manual #2 - Ice Fang (2004)
  • Weird War II Mission Manual #3 - Gods of Destruction (2005)
  • Weird War II Mission Manual #4 - Demonic Artillery (2005)

Pirate Press[edit]

Setting[edit]

  • The Battle for Oz (2014; PDF, hardcover, and softcover)

Reality Blurs[edit]

Setting[edit]

Seeds Of Terror Pdf

  • Runepunk (2007; hardcover)
  • Ravaged Earth: The World of High-Powered Pulp (2008; softcover, regular and deluxe (color) editions)
  • Runepunk: Darksummer Nights (2009; softcover)
  • Runepunk: Steam & Shadow (2009; PDF)
  • Agents of Oblivion: Player's Guide (2009; PDF)
  • Realms of Cthulhu (2009; hardcover)
  • Iron Dynasty: Way of the Ronin (2010; softcover)
  • Agents of Oblivion - The Perfect Cocktail of Horror and Espionage (2011; PDF and softcover)
  • Ravaged Earth: Revised Second Edition (2013; PDF and softcover)
  • Karthador: Swashbuckling Science Fiction (2013; softcover)

Adventures[edit]

  • Agents of Oblivion: Starfall Jungle (2005, PDF)
  • Iron Dynasty: Journey to Red Temple (2005, PDF)
  • Relics & Rumors #1 (2009, PDF)
  • Relics & Rumors #2 (2009, PDF)
  • Amazing Exploits #1: Quest for the Lost Oasis (2009, PDF)
  • Old School Fantasy #1: A Keg For Dragon (2010, PDF and softcover)
  • Relics & Rumors #3 (2010, PDF)
  • Relics & Rumors #4 (2010, PDF)
  • Old School Fantasy #2: Darkness Over Keryhk Nhor (2010, PDF and softcover)
  • Old School Fantasy #3: Hunger of the Iron Mage' (2010, PDF and softcover)
  • Mythos Tales #1: Belly of the Beast (2011, PDF)
  • Iron Dynasty: Kesshi Tales #1: The Wise Men & The Woods (2011, PDF)
  • Iron Dynasty: Kesshi Tales #2: The Demon's Heart (2011, PDF)
  • Iron Dynasty: Kesshi Tales #3: Fresh Blood (2011, PDF)
  • Runepunk: Jobbers Tales #1: Whither Be Witherspoon? (2011, PDF)
  • Old School Fantasy #4: Slave Pens of Moss Stone (2011, PDF)
  • Old School Fantasy #5: Call of the Crow (2011, PDF)
  • Old School Fantasy #6: Tangle in the Silver Vines (2011, PDF)
  • Old School Fantasy #7: Rot & Ruin (2011, PDF)
  • Old School Fantasy #8: Light & Dark (2011, PDF)
  • Old School Fantasy #9: Hand of the Harbinger (2011, PDF)

Source books[edit]

  • Powers & Perils: Orwell Industries (2006, softcover)
  • Iron Dynasty Guidebook #1: Ikusa Kokoro (2011, PDF)
  • Iron Dynasty Guidebook #2: Sorimizu (2011, PDF)
  • Iron Dynasty Guidebook #3: Uma-Ko Ryoudo (2011, PDF)
  • Runepunk Guidebook #1: GreyMesa (2011, PDF)

Ronin Arts[edit]

Source book[edit]

  • Starships! (2005)

Savage Mojo[edit]

Settings[edit]

  • Shaintar: Immortal Legends - Player's Guide (2005; softcover)
  • Savage Suzerain (2009; hardcover)
  • Savage Suzerain Player's Guide (2009; PDF)
  • Suzerain - Dogs of Hades (2010; hardcover)
  • Suzerain - Noir Knights (2010; hardcover)
  • Suzerain - Shanghai Vampocalypse (2010; PDF)
  • Suzerain - Caladon Falls (2010; PDF)
Seeds of terror pdf free download pc

Silver Gryphon Games[edit]

  • Wellstone City (2010; PDF)
  • Wellstone City Chronicles - Two Bit Thugs (2010; PDF)
  • Wellstone City Chronicles - Burning Crosses(2010; PDF)
  • Wellstone City Chronicles - A Death Undeserving (2010; PDF)
  • Camp Wicakini (2010; PDF)
  • Wellstone City (2010; softcover)
  • The Pine Ridge Horror (2010; PDF)
  • Zombacalypse (2010; PDF)
  • Zombacalypse (2010; softcover)
  • Wellstone City Chronicles - Schroedinger's Box (2011; PDF)
  • Camp Wicakini - Part II (2011; PDF)
  • Red Blizzard (2012; PDF)
  • Wellstone City Chronicles - The Ranch Raid (2012; PDF)
  • Wellstone City Chronicles - Two Bit Thugs (2012; PDF)
  • Camp Wicakini 3: Wanagi Mato Lives! (2012; PDF)
  • Wellstone City Chronicles - Breaking Murphy (2012; PDF)
  • Wellstone City Chronicles - Wellstone City Encounter Deck (2011; PDF)

Sneak Attack Press[edit]

  • Broken Earth (2014; PDF and hardcover)

12 to Midnight, Inc.[edit]

Adventures[edit]

  • Last Rites of the Black Guard (2003)
  • Weekend Warriors (2004)
  • Bloodlines (2004)
  • Innana's Kiss (2004)
  • Brainwashed (2005)
  • Skinwalker (2006)
  • Jerry's Midnight Tales (2006)
  • Fire in the Hole (2006)
  • The Beast Within (2007)
  • Chickens in the Mist (2007)

Source books[edit]

  • Green's Guide to Ghosts (2005)
  • Fear Effects (2005)

VampJac Productions[edit]

Setting[edit]

  • Vampire Earth Sourcebook (2005; print-on-demand)

WorldWorks[edit]

Adventures[edit]

  • Something Below (2007)
  • Dinas Fford: The Seeds of War (2007)

References[edit]

  1. ^'Savage Worlds Product Page'. www.peginc.com. Pinnacle Entertainment Group.
Retrieved from 'https://en.wikipedia.org/w/index.php?title=List_of_Savage_Worlds_books&oldid=1029131215'
Phytochemistry, 1972, Vol. 11. pp. 1791 to 1795.
SAPONINS
Pergamon Press.
Printed in England.
OF THE SEEDS OF BASSIA LATIFOLIA
V. HARIHARAN, S. RANGASWAMI and S. SARANGAN Department of Chemistry, University of Delhi, Delhi-7, India (Received 3 September 1971, in revised form 26 October 1971)
Abstract-Two saponins A and B have been isolated from the defatted seeds of Bassia latifolia. The structure of saponin A has been elucidated as 2,3-di-0-glucopyranoside of bassic acid (IV) and that of saponin B as rhamnopyranosyl 1-t 4 xylopyranosyl l+ 2 arabopyranosyl 1-t 00C(28) of saponin A (IX). Bassia latifolia Roxb. Is a large forest tree of Central India. The oil-free seed-cake is used as an insect pois0n.l Earlier investigation by Heywood et aI.= showed the presence of bassic acid in the seeds. During our reinvestigation of this material we have been able to isolate two saponins in pure form and establish their structures. The crude saponin mixture obtained from the defatted seeds by standard methods, when chromatographed over silica gel, yielded two saponins A and B. Saponin A
On acid hydrolysis it gave bassic acid (III), glucose and another substance, compound X. Saponin A reacted with diazomethane to give a monomethyl ester showing that the carboxy of the genin portion was free. Molecular weight determination by micro titration with standard alkali showed that saponin A was a diglucoside and this was supported by its elemental analysis. Saponin A was non-reducing; hence the anomeric hydroxyls should be involved in glycosidic linkages. Saponin A was permethylated by Hakomori’s method,3 the product hydrolysed and the sugar and genin portions examined separately. 2,3,4,6Tetra-O-methylglucose was obtained as the only metbylated sugar fragment; the two glucopyranose units must therefore be attached independently to two different hydroxyl groups of bassic acid. The partially methylated genin fragment resulting from the hydrolysis reacted with periodate, showing the presence of free vicinal hydroxyl groups. It was identified as the 23-methyl ether of methyl bassate (II) by direct comparison with an authentic sample which was prepared by methylating the acetonide of methyl bassate (I) and hydrolysing the product with acid. Therefore saponin A is 2,3-di-0-glucopyranoside of bassic acid. The cotigurations of the linkages were deduced by the application of Hudson’s rule (using Klyne’s4 simplified method). The calculations are shown in Table 1. Hence both glucose units are p-linked. This was confirmed by hydrolysing the saponin with emulsin when D-glucose and bassic acid were formed. The structure of saponin A may therefore be represented by (IV). ’ R. N. CHOPRA, Indigenous Drugs of India, p. 357, Dhur, India (1958). 2 B. J. HEYWOOD. G. A. R. KON and L. L. WARE.J. Chem. Sot. 1124 (1939). , , 3 S. HAKOMORI, i. Biochem. 55,205 (1964). ’ 4 W. KLYNE,Biochem. J. 47,41 (1950). 1791
V.HARMARAN,S.RANGASWAMI
and S. SARANGAN
(III,R=H (IT) R=Glc
Compound X
Compound X referred to above was obtained in larger yield when saponin A was subjected to mild acid hydrolysis. It was acidic and it formed an ester with diazomethane. On further hydrolysis with 7% HzS04 it gave glucose and bassic acid. Its hydrolysis was never complete since even after refluxing with 10% H$04 for 12 hr some starting material was still present. A similar difficulty in hydrolysis had been noted earlier in the case of alfalfa saponin.5 Analyses of X and its methyl ester acetate showed that it was a monoglucoside. The NMR spectrum of the ester acetate showed the presence of six acetoxyl groups which supported the conclusion that it is a monoglucoside. Permethylation followed by acid hydrolysis gave 2,3,4,6-tetra-O-methylglucose as expected. Of the three hydroxyl groups which are available for the attachment of the sugar unit, that at C-23 was ruled out for the following reason. Compound X was treated with periodate and then hydrolysed with HzS04, when bassic acid was formed. Had the sugar been attached to the hydroxyl at C-23 the genin would have been destroyed by periodate. This leaves structures (V) and (VII) as 5 R.J. MORRIS,W. B. DYE and P. S.GISLER,J. Org.
Chem.26, 1241(1961).
1793
Saponins of the seeds of Bassia latifolia TABLE 1. ROTATORYVALUESFORSAPONINA
Substance
l&J (“)
Observed values Saponin A Bassic acid [Ml, contribution of glucose units Literature values 2 x fi-methyl-D-glucocopyranoside’ 2 x a-methyl-D-glucopyranoside6
+35.0 -l-82.1
MID (“1 +284 +399 -115 -124 +624
two alternatives. When saponin X methyl ester was subjected to Jones’ oxidation and the product hydrolysed with acid, a complex mixture resulted. Under these conditions the product should be either (VI) or (VIII) if the structure of X is (V) or (VII) respectively. The crude reaction mixture did not show any W absorption for the presence of a-&unsaturated carbonyl; on the other hand it was acidic. Examination of the alkalisoluble portion by TLC both before and after treatment with diazomethane showed that the spot which constituted the major compound before treatment disappeared and a new major spot with much higher R, appeared. This indicated that the product was probably VIII but it could not be characterized further. Hence in compound X the glucose is most probably attached to the 3-position. Saponin
B
On complete hydrolysis with 7% HzS04, it gave bassic acid, glucose, arabinose, xylose and rhamnose. It was inert towards diazomethane showing that the -COOH at C1, was blocked. When hydrolysed with 2% HzS04, it gave, among other products, saponin A. Thus saponin B is composed of saponin A with additional sugars. When the ester linkage was cleaved with 15 % alkali and the prosaponin esterified with diazomethane, the product was identical with saponin A methyl ester. This clearly showed that saponin B carries arabinose, xylose and rhamnose units on its -COOH group and that-the glucose units on ring A are not carrying any additional sugars nor is there any sugar attached to the OH at C-23. A quantitative estimation of sugars showed the ratio of xylose : arabinose : rhamnose to be 1: 1: 1; the complete hydrolysis of the glucose units being difficult, the estimation of this sugar was omitted. Saponin B was permethylated and hydrolysed. The partial methyl ethers of sugars were identified by paper chromatography (see Experimental) as 3,4-d&0methylarabinose, 2,3-di-0-methylxylose, 2,3,4-tri-O-methylrhamnose and 2,3,4,6-tetra-Omethylglucose. From the permethylation results, it is clear that rhamnose is an end sugar without any branching and is in pyranose form and that arabinose and xylose are inner sugars in the sugar chain and do not have any branching. The mixture of partial methyl ethers obtained from permethylated saponin B was treated with periodate and then examined whereupon the partial methyl ether of arabinose was found to be missing; this confirmed that the arabinose derivative is its 3,4- and not its 2,3-d&O-methyl ether and that this sugar is in the pyranose form. The absence of any partial methyl ether of glucose other than 2,3,4,6-tetra-O-methylglucose together with the fact that there is no branching in the ester sugar chain showed that glucose is not present in the ester sugar chain. It has already been shown that glucose, rhamnose and arabinose are in pyranose form. 6 Dictionary of Organic Compounds (edited by I. Vol. 1, p. 826, Eyre & Spottiswoode, PHYTO11/5--a
HEILBRON,A. H. COOK,H. M. BUNBURYand D. H. HEY),
London (1965).
1794
V. HARIHARAN,S. RANGASWAWand S. SARANGAN
Xylose can be in either furanose or pyranose form, but since furanoxylose is very unusual among natural glycosides, it may be assumed that in saponin B the xylose unit is also in pyranose form. In another experiment saponin B permethylate was reduced with LiAIH, the product hydrolysed and the sugar portion examined by paper chromatography. The spot due to 3,4-di-O-methylarabinose was missing showing that arabinose is the sugar directly linked to the -COOH. Hence the structure of saponin B can be written as (IX), in which the D- or L-nature of the three sugars constituting the triose moiety in ester linkage at C, of the aglycone is not completely established. EXPERIMENTAL
For paper chromatography, Whatman No. 1 paper and the following solvents were employed: n-BuOHHOAc-H20, 4: 1:.5 upper layer (A); n-BuOH-pyridine-HnO, 6:4:3 (B); n-BuOH-pyridine-H&-benzene, 5 : 3 : 3 : 1 (upper layer) (C) ; n-BuOH-EtOH-HtO, 5 : 1: 4 upper layer (D) ; n-BuOH-EtOH-HzO, 3:l:l (E). Isolation of saponiru. The defatted seeds were extracted with alcohol and the extract concentrated to a syrup. It was macerated with ether and the residue was worked up for saponins by the n-BuOH method when a yellow powder was obtained. This was chromatographed over silica gel. Elution with CHCI,-MeOH (92: 8) gave saponin A and with CHC&-MeOH (4: 1) gave saponin B. Saponin A (IV). M.p. 216-218”(d), [aIn f35.0” (c, 0.8 in pyridine) (Found: C, 62.1; H, 8.6. C4ZH66015 requires: C, 62-2; H, 8.2%). Hydrolysis of(IV). It was refluxed with 7 % H2S04 in 80 “/;:aq. MeOH for 6 hr. After addition of water and removal ofsolvent the genin was filtered andchromatographed over silica gel. CHCI,-MeOH (19: 1) eluate gave a pure acid, m.p. > 310”, [a]n +82-l” (c, l-15 in pyridine) (Found: C, 74.1; H, 9.8. C30H46O5 requires: C, 74.1; H, 95%); methyl ester, m.p. 222-224”, [a], f 60.0” (c, 1.11 in pyridine) (Found: C, 73.8; H, 9.6. C3iI&05 requires: C, 74.4; H, 9.6%); acetyl methyl ester, m.p. 148-150”, [ah, C68.2” (c, 124 in CHCI,). Comparison with authentic samnles of bassic acid and methyl bassate showed their identity (m.m.p., TLC and IR). CHC&MeOH, (92: 8) eluate in this chromatogram gave a small amount of substance X, The aqueous mother liquor when examined after neutralization showed the presence of glucose (PC, solvents A-C). Permethylation of (IV) and hydrolysis. Sodium hydride dispersion in oil (50x, 20 mg) was added to a solution of (IV) (20 mg) in dimethyl sulphoxide (DMSO) (2 ml) and the mixture was kept at 80” for 1 hr. After cooling Me1 (0.5 ml) was added and the mixture left overnight. The product was poured into ice-cold Hz0 and extracted with CHC13. The syrup obtained on evaporation of the solvent was permethylated two more times and resulting product which was homogeneous according to TLC was hydrolysed using 7 % aq. methanolic H2S04. MeOH was removed after adding water. The precipitated genin was filtered and purified by chromatography over neutral alumina, m.p. 159-161”, [a]n +61.3” (c, 1.20 in CHCI,) (Found: C, 742; H, 95. C32H5005 requires: C, 74.7; H, 9-7 %.) It reacted with periodate to give a carbonyl compound (TLC, spray DNPH) and it was identified as 23-methyl ether of methyl bassate (II) (described later) (m.m.p., TLC and IR). The aqueous mother liquor was neutralized (BaCO,) and examined for methylated sugars when 2,3,4,6-tetra-0-methylglucose was identified (direct comparison with authentic sample by PC in solvent D). PartiaI synthesis of 23-methyl ether of methyl bassate. To a solution of methyl bassate (150 mg) in dry acetone p-toluene sulphonic acid (1 mg) was added. After keeping for 4 hr at room temp. the product (acetonide (I)) was worked up and puritied by column chromatography over neutral alumina, m.p. 206.207”, [a]n +74.0” (c, 1.00 in CHCI,) (literature m.p. 206-208”).7 IR (KBr): 1170,1156,1096,1047,1036,860 cm-‘. The above acetonide was methylated using CHBI and NaH in DMSO exactly as described under permethylation of (IV). The product (23-methyl ether of methyl bassate 2,3,-acetonide) after purification by column chromatography (neutral alumina) was crystallized from MeOH as flat prisms, m.p. 165-167”, [a]n +86” (c, 1.00 in CHC13). On heating with HCI at 80” for 1 hr the above product gave 23-methyl ether of methyl bassate, m.p. 160-162”, [a]n +66*7” (c, 1.70 in CHC&) (Found: C, 74.2; H, 10.2; 0CH3, 11.7. &Hs005 requires: C, 74.7; H, 9.7; OCH3(2), 12.1%). NMR values in CDCI,: 6 3.65,3H (COOCH,), 6 3.42,3H (CH20C&). Enzymatic hydrolysis of (IV). (IV) (15 mg) in 10 % aq. MeOH (3 ml) was treated with almond emulsion, a few drops of toluene added and the mixture kept at 37”. After 7 days the genin was worked up and found to be a mixture of saponin A, compound X and bassic acid (TLC); the sugar was glucose. Preparation of compoundX. (IV) was hydrolysed with 2 % H,SO, and the genin portion chromatographed over silica gel. Compound X was obtained in major amounts and bassic acid in minor amounts. Compound 7 T. J. KING and J. P. YARDLEY,J. Chem. Sot. 4308 (1961).
Saponins of the seeds of Bassia latifolia
1795
X, m.p. 162-164”, [a]u +60-4” (c, 140 in pyridine) (Found: C, 66.2; H, 9.0. C36H56010 requires: C, 66.7; H. 8.6%): methyl ester m.p. 215”(d), [aID +42*3” (c. 0.90 in pyridine): methyl ester acetate, m.p. 142-144”. [& +.37.4” (c, i-10 in CHCl,) (Found: C, 64.8; H, 8.0. &,&016 requires: C, 64.2; H, 7.6%). Hvdrolvsis of ComDoti X. This was done using 7 % H2SOa in 80 “/, aa. MeOH. The genin was extracted with EtlOVand chromatographed over silica gel. CHdl&%cOH (19: 1) elite gave bassic acid and CHCIJMeOH (92: 8) gave compound X. The aqueous mother liquor contained glucose (PC in solvents A-C). Periodate oxidation of compound X and hydrolysis. Compound X was treated with excess of NaI04 in MeOH for 48 hr at room temp. The product was worked up by extracting with n-BuOH and hydrolysed using 7 % aq. H2S04. The genin was identical with bassic acid. Oxidation of compound X methyl ester and hydrolysis. This was done using Jones’ reagent and the product was extracted with n-BuOH. The butanol extract was washed neutral and evaporated. The brown residue was hydrolysed with 7 ‘A H$SO., in aq. methanol and the product extracted with ether. On removing the solvent a light reddish residue was obtained from which no homogeneous compound could be obtained. Saponin B (Ix). M.p. 212-214”, [a]u -30” (c, 150 in pyridine) (Found: C, 54.1; H, 7.5. C58H98030 requires : C, 54.6 ; H, 7.7 %). Hydrolysis of (IX) with 7 % H2S04. This was done exactly as described under (IV) and the genin portion chromatographed over silica gel, when bassic acid and a small amount of compound X (TLC) were obtained. The aqueous mother liquor was neutralized (BaC03) and examined by PC in solvents A-C; glucose, arabinose, xylose and rhamnose were identified. The compound X was produced in greater yield when saponin B was hydrolysed with 2 % H2S04. Hydrolysis of (IX) with 15 % KOH. (IX) (50 mg) was heated with 15 % aq. KOH (15 ml) at 80” for 45 min. After acidification it was extracted with n-BuOH, the butanol extract neutralized and evaporated. The residue was treated with ethereal CHzN2 and the product crystallized from MeOH-EtzO. It was identical with saponin A methyl ester (m.p., m.m.p., TLC and IR). Quantitative sugar estimation. A known quantity of (IX) was hydrolysed with Kiliani mixture (HOAcHCl-H20, 7:2: 11) at 100” for 6 hr in a sealed tube. The sugar portion was chromatographed on paper, sprayed with aniline hydrogen phthalate, the sugar spots eluted with 60 ok aq. HOAc and estimated colorimetrically. Permethylation of (IX) and hydrolysis. This was carried out using CH31 and NaH in DMSO and the product was hydrolysed with Kiliani mixture. The methylated sugars were identified by PC. Authentic 2,3,4,6-tetra-O-methyl-D-glucose, 2,3,4-tri-0-methyl-L-rhamnose and 2,3,4-tri-O-methyl-r.-arabinose, were used as standards. The Rc values of the four spots obtained with solvent D were l-01, 1.00, 0.72 and 0.59 (RG of authentic 2,3,4,6-tetra-O-methyl-u-glucose is taken as 1) and the RAr values of the four spots obtained with E were 1.18, 1.17, 0.92 and 0.72 (RAr of authentic 2,3,4-tri-0-methyl+arabinose is taken as 1). The Rc values of the first three spots in D are, according to literature,* those of 2,3,4tri-0-methyl+rhamnose, 2,3,4,6-tetra-O-methyl-D-glucose and 2,3-di-O-methyl-n-xylose; the first two spots also compared well with standard substances; the fourth and slow moving spot (RG 0.59) could not be identified, but it cannot be due to 2,3-di-0-methyl-arabinose whose Rc according to literature” should be 064. Again, the first two spots in E are those of 2,3,4-tri-0-methylrhamnose and 2,3,4,6-tetra-o-methylglucose (direct comvarison with authentic samvles) and the spot with RAr 0.72 should be due to 3,4-di-Omethylarabinose whose RAr according to literatmegshould be 6.72. The fourthspotinE (RAr0.92)isevidently derived from the xylose moiety. When the mixture of partial methyl ethers was treated first with periodate and the product examined subsequently, the spot with RG 0.59 in D and RAr 0.72 in E alone was absent. LiAlI& reduction of saponin B permethylate and hydrolysis. Saponin B permethylate (15 mg) was reduced with LiAlH, (20 mg) in boiling tetrahydrofuran (5 ml) for 6 hr. After decomposition of excess of LiAlH, with moist EtOAc the product was acidified and extracted with EtOAc. The solvent was removed, the residue hydrolysed with Kiliani mixture and the sugar portion examined by PC in D. Only three spots with R. values 1.01 (2,3,4-tri-0-methylrhamnose), 1.00 (2,3,4,6-tetra-0-methylglucose) and 0.72 (2,3-di-o-methylxylose) were obtained. Acknowledgements-The authors are grateful to Professor T. R. Seshadri for his kind interest and the Indian Council of Medical Research and the Central Council for Research in Indian Medicine and Homoeopathy for financial assistance. * E. LEDERER and M. LEDERER, Chromatography p. 249, Elsevier, New York (1957). 9 S. C. WILLIAMSand J. K. N. JONES,Can. J. Chem. 45,225 (1967).
Key Word Index-Bassia
Iatifolia seed; Sapotaceae;
saponins;
bassic acid glycosides.