JP2020502040A - 植物源からカンナビノイドを選択的に抽出する方法 - Google Patents
植物源からカンナビノイドを選択的に抽出する方法 Download PDFInfo
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- JP2020502040A JP2020502040A JP2019516149A JP2019516149A JP2020502040A JP 2020502040 A JP2020502040 A JP 2020502040A JP 2019516149 A JP2019516149 A JP 2019516149A JP 2019516149 A JP2019516149 A JP 2019516149A JP 2020502040 A JP2020502040 A JP 2020502040A
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Abstract
Description
ここに開示されている主題の背景として関連があると考えられる参考文献を以下に列挙する。
[1]WO2008/058366
[2]A.Spernath,A.Aserin,コロイドと界面科学の進歩2006,128
[3]A.Spernath,A.Aserin,N.Garti,コロイドおよび界面科学ジャーナル2006,299,900乃至909
[4]A.Spernath、A.Aserin,N.Garti,熱分析と熱量ジャーナル2006,83
[5]N.Garti,A Spernath,A.Aserin,R.Lutz,ソフトマター 2005,1
[6]A.Spernath,A.Aserin,L Ziserman,D.Danino,N.Garti,制御リリースジャーナル 119
[7]S.Fisher,E.J.Wachtel,A.Aserin,N.Garti,コロイドと表面B:Biointerfaces2013,107,35−42
[8]R.Deutch−Kolvzon,A.AserinおよびN.Garti,Chemistry and Physics of Lipids,2011,164(7)654
[9]O.Amsalem,A.Aserin,N.Garti,コロイドと表面,B: Biointerfaces,2010,81(2)422−429。
(a)第1の量のカンナビノイド含有(例えば、CBD含有)植物源と、第1の量の抽出培地とを含む第1の混合物を得るステップであって、この抽出培地が、少なくとも1つの油と、少なくとも1つの共界面活性剤と、選択的に少なくとも1つの共溶媒を含む、ステップと;
(b)第1の混合物を均質化するステップと;
(c)均質化した混合物をバイオマススラリーとカンナビノイド(例えば、CBD)添加培地とに分離するステップ。
− 中鎖トリグリセリド(MCT)、ポリソルベート80(Tween80)、ポリオキシル35ヒマシ油(クレモフォアヒマシ油)、ポリプロピレングリコール(PG)、および少なくとも1つのリン脂質;または
−R−(+)−リモネン、ポリソルベート80(Tween80)、ポリプロピレングリコール(PG)、および エタノールおよびイソプロピルアルコールから選択される少なくとも1つの溶媒;または
− トリアセチン、ポリオキシル35ヒマシ油(クレモフォアヒマシ油)、パルミトステアレート(ラブラソール)、少なくとも1つのリン脂質、及びエタノールおよびイソプロピルアルコールから選択される少なくとも1つの溶媒;または
− 中鎖トリグリセリド(MCT)、スクロースモノ−/ジ−ラウレート、ポリプロピレングリコール(PG)、少なくとも1つのリン脂質、及びエタノールおよびイソプロピルアルコールから選択される少なくとも1つの溶媒;または
− 中鎖トリグリセリド(MCT)、オレイン酸、ポリソルベート80(Tween80)、ポリオキシル35ヒマシ油(クレモフォアヒマシ油)、グリセロール、ポリプロピレングリコール(PG)、少なくとも1つのリン脂質、およびエタノールおよびイソプロピルアルコールから選択される少なくとも1つの溶媒。
(d)バイオマススラリーを第2の量の抽出培地と混合して第2の混合物を得るステップと;
(e)第二混合物を均質化するステップと;
(f)第2の混合物をバイオマススラリーと高カンナビノイド添加培地に分離するステップ。
(d’)カンナビノイド添加培地を第2の量の植物源と混合して第2の混合物を得るステップと;
(e’)第二混合物を均質化するステップと;
(f’)第2の混合物をバイオマススラリーと高カンナビノイド添加培地に分離するステップ。
上述したように、CBDの少なくとも一部はCBDAの形で植物中に見られる。CBDAの脱カルボキシル化は、制御された条件下で植物を加熱することによって実施でき、所望のCBDを得ることができる。以下の実施例で使用した植物は、大麻サティバと大麻インディカの様々な雑種である。
上述したように、抽出プロセスに使用される抽出培地は、自発的に形成される自己組織化システムである。したがって、抽出培地のいくつかの組成物は、25乃至70℃で成分を単純に混合することによって調製した。抽出培地を調製する例示的な方法は、油、界面活性剤および共界面活性剤(および該当する場合は、溶媒、共溶媒および/またはリン脂質も)を、均質でクリア(透明)な混合物が得られるまで共に混合するステップを具える。界面活性剤または油が室温で固体である場合は、混合しながら加熱して完全に溶解させ、空の抽出培地を形成することができる。
植物サンプルのカンナビノイドプロファイル
本開示の抽出プロセスにおいて、様々なカンナビノイド株を試験した。エタノール抽出(上述の通り)およびHPLC分析によって、抽出培地での抽出の前に植物の試料をカンナビノイドプロファイルについて評価した。様々な株のカンナビノイドプロファイルを表3に示す。
植物サンプル(加熱後)をAX−1抽出培地と1:40の重量比で混合した。次いで、ラボシルバーソンのホモジナイザーL5M−Aを混合物を使用して、30分間、室温で均質化した。均質化の後、各サンプルを4000rpmで20分間遠心分離するか、または綿毛を通して濾過した。試料は3つ調製した。
抽出効率に関する植物対培地の比率の影響は、抽出培地に対する植物源の比率が変化する混合物を分析することによって評価した。
多重抽出法によって抽出培地中のCBD濃度を増加させた。多重抽出法の場合、いくつかの抽出サイクルについて同じ量の抽出培地を使用して多数の抽出サイクルを実施し、各サイクルにおいて以下の手順に従って新鮮な植物試料を抽出する。
特定のカンナビノイド、特にCBDの抽出に対する本明細書に記載されている抽出培地の選択性を実証するために、植物試料をエタノールまたは石油エーテルでも抽出した。両溶媒も公知であり、カンナビノイドの抽出に使用されている。抽出のプロセスは、上述したように、本開示の抽出培地を用いて行ったものと同じであった。
5CSおよびAX2抽出培地(表5−1参照)に5重量%のCBDを添加し、異なる条件下(保護なしで、600ppmの酢酸トコフェロールを添加して、窒素雰囲気下で)、3つの異なる温度(4、25および40℃)でインキュベートした。この濃縮物と希釈マイクロエマルジョン(水80%)の両方を試験した。
5CSおよびAX1抽出培地(上記表1参照)を用いて、以下の手順に従って植物源からCBDを抽出した。1:15w/w比の植物:ME、200℃で均質化下させて、抽出時間30分。抽出サイクルを2回実施し、各サイクルについて試料を収集した。試料を3つの異なる温度(4、25および40℃)で70日間インキュベートした。試料は希釈しなかった(すなわち、濃縮試料について試験を行った)。
薬物動態(PK)プロファイルは、AX−1および5CSのCBD添加製剤を経口投与した後に血漿中のCBD濃度を、オリーブ油に可溶化させたCBDと比較して測定することによって評価した。
痛みへの反応
本開示の抽出大麻植物源(CBD添加)培地の、マウスにおける痛みに対する反応および抗炎症活性を、5CS抽出培地を用いて大麻植物からの抽出物の経口投与によって、伝統的なエタノール抽出と比較して評価した。
CBDは炎症反応を減少させ、炎症反応により痛みを受けることが示された。理論に縛られることを望まないが、炎症の減少は、CB1受容体、アデノシン受容体およびその他のGPCRへのアゴニストおよびアンタゴニスト結合を含む様々なメカニズムによって達成される。これは、IL−2、IL−6、TNF−α、MCP−1などの炎症性サイトカインやケモカインレベルの減少を含む。
Claims (53)
- 植物源からのカンナビノイドの抽出方法において:
(a)第1の量のカンナビノイド含有植物源と第1の量の抽出培地を含む第1の混合物を得るステップであって、前記抽出培地が少なくとも1つの油と、少なくとも1つの親水性界面活性剤と、少なくとも共界面活性剤を含むステップと;
(b)前記第一の混合物を均質化するステップと;
(c)前記均質化した第一の混合物をバイオマススラリーとカンナビノイド添加培地とに分離するステップと;
を具えることを特徴とする方法。 - 前記カンナビノイドがカンナビジオール(CBD)であることを特徴とする請求項1に記載の方法。
- 前記植物源が少なくともCBDと、テトラヒドロカンナビノール(THC)を含むことを特徴とする請求項1または2に記載の方法。
- 使用済みバイオマスがTHCに富んでおり、前記CBD添加培地が最大で3重量%のTHCを含み;選択的に、最大2重量%のTHC、最大1重量%のTHC、最大0.8重量%のTHC、最大0.6重量%のTHC、最大0.5重量%のTHC、または最大0.1重量%のTHC、を含むことを特徴とする方法。
- 前記カンナビノイド添加培地が約0.1乃至12重量%のCBDを含むことを特徴とする、請求項1乃至4のいずれか1項に記載の方法。
- 前記植物源が大麻属由来の植物であることを特徴とする、請求項1乃至5のいずれか1項に記載の方法。
- 前記植物源が、大麻サティバ、大麻インディカ、大麻ルデラリス、およびこれらの任意の混合物から選択されることを特徴とする、請求項6に記載の方法。
- 前記植物源が、大麻の花、花序、芽、果実、果皮、種子、葉、茎(stem)、柄(stalk)、根、およびこれらの任意の混合物から選択されることを特徴とする、請求項6または7に記載の方法。
- 前記植物源が、粉末、顆粒、ペレット、錠剤、または植物部分の形態で提供されることを特徴とする、請求項1乃至8のいずれか1項に記載の方法。
- 前記ステップ(b)の均質化が、約1分乃至60分の間にわたって行われ;選択的に約1分乃至60分の間、約1分乃至45分の間 、約1分乃至30分の間、または約1分乃至20分の間行われることを特徴とする、請求項1乃至9のいずれか1項に記載の方法。
- 前記ステップ(b)の均質化が約500乃至5000psiの間の圧力で行われることを特徴とする、請求項1乃至10のいずれか1項に記載の方法。
- 前記ステップ(b)の均質化が、約5−70℃の温度で行われることを特徴とする、請求項1乃至11のいずれか1項に記載の方法。
- 前記混合物を分離するステップが遠心分離によって行われることを特徴とする、請求項1乃至12のいずれか1項に記載の方法。
- 前記混合物を分離するステップが、遠心分離とそれに続く濾過によって行われることを特徴とする、請求項13に記載の方法。
- 前記ステップ(a)の前に、前記植物源を加熱するステップをさらに具えることを特徴とする、請求項1乃至14のいずれか1項に記載の方法。
- 前記植物源が約90乃至180℃の温度に加熱されることを特徴とする請求項15に記載の方法。
- 前記植物源が、約5乃至240分の間加熱されることを特徴とする、請求項15または16に記載の方法。
- 前記植物源と前記第1の量の抽出培地との重量比(wt/wt)が1:5乃至1:100であることを特徴とする、請求項1乃至17のいずれか1項に記載の方法。
- 請求項1乃至18のいずれか1項に記載の方法がさらに:
(d)バイオマススラリーを前記第2の量の抽出培地と混合して第2の混合物を得るステップと;
(e)前記第2の混合物を均質化するステップと;
(f)前記第2の混合物を、バイオマススラリーとカンナビノイド添加培地に分離するステップと;
を具えることを特徴とする方法。 - 前記ステップシーケンス(d)乃至(f)を1乃至7回繰り返すことを特徴とする、請求項19に記載の方法。
- 請求項1乃至18のいずれか1項に記載の方法がさらに:
(d’)前記カンナビノイド添加培地を第2の量の植物源と混合して第2の混合物を得るステップと;
(e’)前記第2の混合物を均質化するステップと;
(f’)前記第2の混合物をバイオマススラリーと高CBDカンナビノイド添加培地とに分離するステップと;
を具えることを特徴とする方法。 - 前記ステップシーケンス(d’)−(f’)を1乃至7回繰り返すことを特徴とする、請求項21に記載の方法。
- 前記少なくとも1つの油が、精油、D−リモネン、鉱油、パラフィン系油、リン脂質、極性脂質、スクアレン、スピンゴメリン、ワックス、植物油、グリセリド、トリグリセリド、脂肪酸および脂肪酸エステル、ならびに液体炭化水素から選択され;選択的に、前記少なくとも1つの油が、約0.5乃至20重量 %の間の量で抽出培地中に存在する、ことを特徴とする請求項1乃至22のいずれか1項に記載の方法。
- 前記少なくとも1つの親水性界面活性剤が、ソルトールHS15、ポリオキシエチレン、ソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノオレエート、および飽和および不飽和ヒマシ油のポリオキシエチレンエステル、パルミトステアリン酸、エトキシル化モングリセロールエステル、エトキシル化脂肪酸、短鎖、中鎖および長鎖エトキシル化脂肪酸、から選択され:選択的に、前記少なくとも1つの親水性界面活性剤が、約30乃至85重量%の量で抽出培地中に存在することを特徴とする請求項1乃至23のいずれか1項に記載の方法。
- 前記少なくとも1つの共界面活性剤が、ポリプロピレングリコール、ポリエチレングリコール、ソルビトール、キシリトール、PEG200、PEG400およびPEG600から選択され、選択的に、前記少なくとも1つの共界面活性剤が、抽出培地中に約1乃至50重量%の量で存在する、ことを特徴とする請求項1乃至24のいずれか1項に記載の方法。
- 前記抽出培地がさらに少なくとも1つのリン脂質を含み、選択的に前記抽出培地が約1乃至10重量%のリン脂質を含むことを特徴とする、請求項1乃至25のいずれか1項に記載の方法。
- 前記抽出培地がさらに、エタノール、プロパノール、イソプロパノール、酢酸、および乳酸から任意に選択される少なくとも1つの溶媒を含み、選択的に、前記抽出培地が約0.1乃至25重量%の前記溶媒を含むことを特徴とする、請求項1乃至26のいずれか1項に記載の方法。
- 前記均質化した混合物が油滴を含み、当該油滴内に(または油滴の界面に)前記カンナビノイドが幾何学的および物理的に一体化されていることを特徴とする、請求項1乃至27のいずれか1項に記載の方法。
- カンナビノイド含有植物源からカンナビノイドを選択的に抽出するための抽出培地において、少なくとも1つの油、少なくとも1つの親水性界面活性剤、および少なくとも1つの共界面活性剤を含み、前記抽出培地が選択的に、少なくとも一つのリン脂質、少なくとも1つの溶媒、および/または、少なくとも1つの共溶媒をさらに含むことを特徴とする抽出培地。
- カンナビノイドがカンナビジオール(CBD)であることを特徴とする、請求項29に記載の抽出培地。
- 請求項1乃至28のいずれか1項に記載の方法によって得られるカンナビノイド添加培地。
- 前記少なくとも1つの油が、精油、D−リモネン、オレイン酸、トリアセチン、鉱油、パラフィン油、リン脂質、極性脂質、スクアレン、スピンゴメリン、ワックス、植物性油、グリセリド、トリグリセリド、脂肪酸および脂肪酸エステル、ならびに液体炭化水素から選択され、選択的に、前記少なくとも1つの油が、前記培地中に約0.5乃至20重量%の量で存在することを特徴とする、請求項31に記載のカンナビノイド添加培地。
- 前記少なくとも1つの親水性界面活性剤が、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノオレエート、および飽和および不飽和ヒマシ油のポリオキシエチレンエステル、エトキシル化モノグリセロールエステル、グリセロール、短鎖、中鎖、長鎖脂肪酸のエトキシル化脂肪酸から選択され、選択的に、前記少なくとも1つの親水性界面活性剤が前記培地中に約30乃至85重量%の量で存在する、ことを特徴とする請求項31または32に記載のカンナビノイド添加培地。
- 前記少なくとも1つの共界面活性剤が、ポリプロピレングリコール、ポリエチレングリコール、ソルビトール、キシリトール、PEG200、PEG400およびPEG600から選択され、選択的に、前記少なくとも1つの溶媒が、培地中に約1乃至50重量%の量で存在することを特徴とする請求項31乃至33のいずれか1項に記載のカンナビノイド添加培地。
- 前記培地が、約1乃至10重量%のリン脂質を含むことを特徴とする、請求項31乃至34のいずれか1項に記載のカンナビノイド添加培地。
- エタノール、プロパノール、イソプロパノール、酢酸、および乳酸から選択される少なくとも1つの溶媒をさらに含み、選択的に前記培地が約0.1乃至25重量%の前記溶媒を含むことを特徴とする請求項31乃至35のいずれか1項に記載のカンナビノイド添加培地。
- 前記カンナビノイドがカンナビジオール(CBD)であることを特徴とする、請求項31乃至36のいずれか1項に記載のカンナビノイド添加培地。
- 約1乃至12重量%の間のCBDを含むことを特徴とする、請求項37に記載のカンナビノイド添加培地。
- 最大で3重量%のTHCを含むことを特徴とする、請求項37または38に記載のカンナビノイド添加培地。
- 前記カンナビノイドが、幾何学的および物理的に前記油と一体化されていることを特徴とする、請求項31乃至39のいずれか1項に記載のカンナビノイド添加培地。
- 少なくとも0.1重量%のCBD、少なくとも1つの油、少なくとも1つの親水性界面活性剤、および少なくとも1つの共界面活性剤を含み、選択的に少なくとも1つのリン脂質、少なくとも1つの溶媒、および少なくとも1つの共溶媒を含むことを特徴とするCBD添加培地。
- 請求項31乃至40のいずれか1項に記載のカンナビノイド添加培地または請求項41に記載のCBD添加培地を含むことを特徴とする、食品、栄養補助食品、または栄養補助食品組成物。
- 請求項31乃至40のいずれか1項に記載のカンナビノイド添加培地または請求項41に記載のCBD添加培地を含むことを特徴とする医薬組成物。
- ゲル、ローション、油、石鹸、スプレー、エマルジョン、クリーム、軟膏、カプセル、ソフトゲルカプセル、パッチ、または溶液から選択される形態であることを特徴とする、請求項43に記載の医薬組成物。
- カンナビノイドを局所的に、経口的に、吸入により、経鼻的に、経皮的に、眼内に、または非経口的に対象の循環系に送達するように構成したことを特徴とする、請求項43または44に記載の医薬組成物。
- 少なくとも1つの希釈剤を含むことを特徴とする、請求項42乃至45のいずれか1項に記載の医薬組成物。
- 前記カンナビノイド添加培地が前記希釈剤によって希釈され、それによって希釈剤マトリックス内に油滴を形成することを特徴とする、請求項46に記載の組成物。
- 前記カンナビノイドが、前記油滴のオイルコア内に、または前記油滴と希釈剤マトリックスとの界面と、幾何学的および物理的に一体化されていることを特徴とする、請求項47に記載の医薬組成物。
- 痛み関連障害、炎症性の障害および症状、アパタイトの抑制または刺激、嘔吐および悪心の症状、腸およびボウルの障害、不安神経症に関連する障害および症状、精神病に関連する障害および症状、発作および/または痙攣に関連する障害および症状、睡眠障害および症状、免疫抑制による治療を必要とする疾患、障害および症状、血糖値の上昇に関連する疾患および症状、神経系の悪化に関連する障害および症状、炎症性皮膚の障害および症状、動脈閉塞に関連する障害および症状、細菌感染に関連する障害および症状、真菌感染に関連する障害および症状、増殖性の障害および症状、外傷後の障害、および骨成長の抑制に関連する障害および症状、から選択される状態の治療に使用する、請求項31乃至40のいずれか1項に記載のカンナビノイド添加培地、請求項41に記載のCBD添加培地、または請求項43乃至48のいずれか1項に記載の医薬組成物。
- ある症状または障害を患っている対象を治療する方法において、請求項31乃至40のいずれか1項に記載のカンナビノイド添加培地、請求項41に記載のCBD添加培地、または、請求項43乃至48のいずれか1項に記載の医薬組成物培地を対象に投与するステップを具えることを特徴とする方法。
- 前記症状または障害が、痛み関連障害、炎症性の障害および症状、アパタイトの抑制または刺激、嘔吐および悪心の症状、腸およびボウルの障害、不安神経症に関連する障害および症状、精神病に関連する障害および症状、発作および/または痙攣に関連する障害および症状、睡眠障害および症状、免疫抑制による治療を必要とする疾患、障害および症状、血糖値の上昇に関連する疾患および症状、神経系の悪化に関連する障害および症状、炎症性皮膚の障害および症状、動脈閉塞に関連する障害および症状、細菌感染に関連する障害および症状、真菌感染に関連する障害および症状、増殖性の障害および症状、外傷後の障害、および骨成長の抑制に関連する障害および症状、から選択されることを特徴とする、請求項50に記載の方法。
- 植物源からCBDを抽出する方法において:
(a)第1の量のCBD含有植物源と、第1の量の抽出培地とを含む第1の混合物を得るステップであって、前記抽出培地が少なくとも1つの油、少なくとも1つの親水性界面活性剤および少なくとも1つの共界面活性剤を含むステップと;
(b)前記第1の混合物を均質化するステップと;
(c)前記均質化された第1の混合物をバイオマススラリーとCBD添加培地とに分離するステップと;
を具えることを特徴とする方法。 - CBD含有植物源からカンナビジオール(CBD)を選択的に抽出する抽出培地において、少なくとも1つの油、少なくとも1つの親水性界面活性剤、および少なくとも1つの共界面活性剤を含み、前記抽出培地が、選択的に、少なくとも1つのリン脂質、少なくとも1つの溶媒、および/または、少なくとも1つの共溶媒をさらに含むことを特徴とする抽出培地。
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US11666618B2 (en) | 2023-06-06 |
IL248150A0 (en) | 2017-01-31 |
WO2018061009A1 (en) | 2018-04-05 |
JP7265264B2 (ja) | 2023-04-26 |
IL248150B (en) | 2018-05-31 |
MX2019003736A (es) | 2019-10-09 |
US20190231833A1 (en) | 2019-08-01 |
AU2017335724B2 (en) | 2023-05-25 |
KR102569534B1 (ko) | 2023-08-22 |
AU2017335724A1 (en) | 2019-05-16 |
BR112019006081A2 (pt) | 2019-06-18 |
EP3518950A1 (en) | 2019-08-07 |
KR20190084036A (ko) | 2019-07-15 |
BR112019006081B1 (pt) | 2023-02-07 |
NZ752820A (en) | 2022-09-30 |
CA3038474A1 (en) | 2018-04-05 |
CN109996551A (zh) | 2019-07-09 |
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